ETA 2026 – Switching from Inclusion to Exclusion Planning for the Estate Tax

Currently (and since the Tax Cuts and Jobs Act of 2017), we, like many other practitioners, have seen an incredible uptick in inclusion planning[1] instead of the traditional exclusion planning (getting assets out of one’s taxable estate). A primary driving force for this major shift was the essential doubling of the estate tax exemption (from…
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Intentionally Defective Grantor Trusts – Have your cake and eat it, too

Shortly before his passing, Benjamin Franklin uttered one of his more infamous quotes, “In this world, nothing is certain except death and taxes.” With the certainty of death implicitly comes another: everyone will transfer his or her wealth, whether in life or after death. How a person transfers wealth will affect how the other certainty,…
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Monetized Installment Sales – Proposed Regulations will Lead to Burdensome Reporting Requirements and Increased Scrutiny

Monetized Installment Sales, as previously written upon by Gray Edmondson,[1] have been subject to increased scrutiny by the IRS in recent years, making its “Dirty Dozen” list in each of the last three years.[2] The IRS remains on the offensive in scrutinizing such transactions, issuing proposed regulation under Internal Revenue Code Section 6011 in August…
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Life Settlements of Life Insurance Policies: What, When, and How

Many individuals take out life insurance policies for valid planning reasons which later are no longer needed or desirable. Alternatively, the policy owner may need current liquidity. While many policies can be surrendered for their cash value or the owner may take loans against the policy, there may be other options. One of those options…
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Threading the Needle – The Utility and Structural Requirements of ING Trusts

Estate planners and tax practitioners have been utilizing incomplete non-grantor trusts, or “ING” trusts, with increased frequency. ING trusts can be utilized for a number of reasons, including, but not limited to, federal income tax planning,[1] asset protection, planning for qualified small business stock benefits, income shifting through distributions to descendants, and others. While this…
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GSS Holdings – A Reminder on Economic Substance and Step Transaction

Most tax law is made up of very detailed statutes, regulations, case law, and other guidance. Layered on top of that body of law are a number of “judicial doctrines” that seek to serve as a backstop to formalistic analyses that could result in unintended tax results, allow taxpayers to place the form of transactions…
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Evaluating the Landscape: Impact of CIC Services, LLC Case on Attorneys’ Fees and Government Fairness

The recent opinion from the United States District Court, Eastern District of Tennessee, continues the saga of the case of CIC Services, LLC (“CIC”) and has implications for taxpayers seeking to recover attorneys’ fees under the Equal Access to Justice Act (“EAJA”) and for its broader reflections on governmental fairness, particularly those looking to challenge…
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Chief Counsel Advice Memorandum Debunks Tax Avoidance Scheme Using Trust

In a recent Chief Counsel Advice Memorandum[1] (“CCM”), the office of the IRS Chief Counsel debunks the income taxation, or lack thereof, found in promotional materials promoting a structure known as a “Non-grantor, irrevocable, complex, discretionary, spendthrift trust”, with a note that the structure may be referred to by several other similar but slightly different…
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Non-Recourse Debt Forgiveness Bites Shareholder Upon Forgiveness

How is relief of debt treated for tax purposes? Does it matter if the debt is recourse or non-recourse? Does it matter if the debtor is a separate entity guaranteed by the owner(s)? Does it matter if the debt is forgiven as part of a sale of property securing the debt? These issues were addressed…
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Directions

[**Practice Alert: Corporate Transparency Act is Here: What You Need to Know**](https://esapllc.com/practice-alert-cta-mar-2024/)
[**Practice Alert: Corporate Transparency Act is Here: What You Need to Know**](https://esapllc.com/practice-alert-cta-mar-2024/)